Metallo-substituted naphthalene

DETAILED DESCRIPTION It is claimed: 1.
Compounds of the formula ##STR4## wherein R is lower alkyl and R.
sub.
1 and R.
sub.
2 are lower alkyl, or aralkyl of 7 to about 12 carbon atoms, and M is MgBr.
2.
The compounds of claim 1 wherein R is methyl.
3.
The compounds of claim 2 wherein R.
sub.
1 and R.
sub.
2 are methyl.




Description:
This invention relates to a method of synthesizing menaquinones, and particularly 3-prenyl-2-alkyl menaquinones.
The invention includes the preparation of 3-metallo-2-alkyl-1,4-di(alkoxy or aralkoxy) naphthalenes, and these intermediates have as the 3-metallo substituent lithium, lithium/copper, copper or magnesium bromide.
The invention provides as novel compounds the intermediates in which the 3-metallo substituent is lithium/copper, copper or magnesium bromide.
According to the invention the 3-metallo intermediates can be reacted with a prenyl halide to prepare the corresponding 3-prenyl-2-alkyl-1,4-di(alkoxy or aralkoxy) naphthalenes, which can be oxidized to the corresponding 3-prenyl-2-alkyl menaquinones.
It is a further aspect of the invention that the oxidation is advantageously conducted by the use of argentic oxide.
The 3-prenyl-2-alkyl menaquinones prepared by this invention have the structural formula: ##STR1## wherein R is alkyl, for instance, lower alkyl, say of 1 to about 4 or 8 carbon atoms, preferably methyl, and wherein Z is --CH.
sub.
2 CH.
dbd.
C(CH.
sub.
3)CH.
sub.
2 ].
sub.
m, --CH.
sub.
2 CH.
sub.
2 CH(CH.
sub.
3)CH.
sub.
2 ].
sub.
n or combinations thereof, and in which each of m and n, and their sum may be 0 to about 25 or more, and frequently, each of m and n and their sum are 0 or 1 to about 9 or 12.
For convenience, these compounds are sometimes hereafter referred to as the MK Compounds or the MK-integer Compounds wherein the integer represents the value of m plus n plus 1.
These compounds have heretofore been designated as being in the vitamin K series, see U.
S.
Pat.
No.
2,348,037, and can be administered to red-blooded animals in the usual manner as vitamin K compounds to combat bleeding